David Powers
Jan 17, 2018 · 6 min read

We have the incredible privilege of working with a lot of entrepreneurs to make The Hum happen. Working with incredibly determined, intelligent, and insightful people each day has its perks. Each Wednesday, we share another piece of what we’ve learned from our journey working with some of the most inspiring people around.


There is no consistency in entrepreneurship. Some people find success nearly immediately, others find it 20 years in. Some people build their first company into a $100M empire, some people fail nine times and then find success the tenth time around. Some people never find success.

Added to this, entrepreneurs by nature have a million ideas spinning in their heads at all times. They could be working primarily on one idea and experimenting with three or four more on the side. If one doesn’t work out, another one subs in.

Plus, millennials have a burning desire to make a lasting impact with their work. And that isn’t always easy.

All of this makes it maddeningly difficult to know when is the right time to get out and when is the right time to dig even deeper.

There is a lot to consider.

Success is misrepresented

How long was Marc Cuban working at the entrepreneurship game before he became successful? What about Elon Musk? Lori Greiner?

I am willing to bet you don’t know that answer for any of them. I don’t either.

That’s because the world’s best entrepreneurs are often misrepresented as overnight success stories. But in reality, many of them fail and fail hard before they ultimately find success.

We recently conducted an interview with Ari Krasner, a Co-Founder of Givebutter, which will run next week. In it, he actually discouraged most people from getting into entrepreneurship. His reasoning is that most people just see the “sexy” side of startups — the money, the success. But what they don’t know is that the people that found that success actually slaved away, ate frozen food, and lost all of their friends for 6 years before they made it.

This misrepresentation is troubling because of our propensity to compare ourselves to other people at all times.

Comparing ourselves to others

We hear stories of entrepreneurs that were (seemingly) extremely successful right away but that may not be us. If we are not an immediate success, it is easy to think our idea blows, or we are in the wrong business, or we aren’t cut out for the entrepreneurial game.

In our own field, theSkimm famously hacked their way to their first 1,000 subscribers on day one and then blew up almost immediately after getting a shout out on the Today Show four days into their business. The Hustle enjoyed similar viral success, hitting 100,000 email subscribers in 5 months.

No matter your industry, there are these crazy success stories that get most of the attention. You don’t hear about the dozens of other companies that enjoyed great success after growing slowly, or the hundreds that are still trying to figure it out, or the thousands that already failed.

This can make it easy to quit too soon. We think if we don’t enjoy viral success, it must be time to hop on to the next idea floating around in our brains.

“I’m just not having an impact.”

Millennial entrepreneurs double down on this dilemma because we are just so damn obsessed with having an impact right away. How dare we.

This video of Simon Sinek discussing millennials in the workplace went viral about a year ago. It was controversial, and opinions split over whether Sinek made a number of remarkable points or was simply picking low hanging fruit to take shots at millennials and sell his new book.

Either way, one part, in particular, stuck with me. Sinek describes the young, motivated professional who approaches him 8 months into their new job and says, “I think I’m going to quit.” Sinek probes as to why and the millennial replies, “I’m just not having an impact.”

This gets a laugh from the crowd. “Of course you aren’t having an impact, you’ve been there for 8 months.”

But I think this question digs a lot deeper and spills over into entrepreneurship. If your company isn’t immediately successful, you not only aren’t having the personal success you seek, you are also not having the impact you desire. How long are you supposed to give it while not having an impact? 8 months? A year? Two years? Ten?

On one hand, it is reasonable to expect you need to work and grind and dig deep for a long period of time to have an impact. But on the other, shouldn’t you be able to have an impact right away?

Think in two-year commitments

Our interview with Matt Daniels, Editor of The Pudding, which ran yesterday provided at least one perspective on the question we are trying to answer. One of his main pieces of advice was the idea that people should think in not one, but two-year commitments.

“When you plant that flag say, ‘I’m going to do this for two years,’ instead of one year or six months because, while you should be ready to fail and choose new things, two years really is the range where the choice has the ability to blossom.

It’s going to take a long time. You need to give it a year. The first year is simply telling everybody what you’re doing and that only pays dividends a year later.”

Matt’s take makes sense but it really only covers a potential minimum. But how long past that do you stick with the same venture?

The answer? Ask questions.

So what’s the answer? When do you get out and when do you dig in?

Maybe how long you stick with a project shouldn’t be based on how successful it is, but rather about your level of passion for that project.

Can you put in 16-hour days and like it?

Would you do this for free? (Maybe you are.)

If you found out your life was going to end in a year, would you spend the rest of it doing what you’re doing?

Is the world going to be better for the work you did today?

If you answered no to those questions, it may be time to get out.

But if you can answer yes for all of these, then dig in. Whether you have been at it for two days, two months, two years, or two decades.

If you are that passionate about it, you will find a way to make it successful. No matter how long it takes.


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The Hum

Stories of what it is really like to start your own business, as it happens, without the rose-colored glasses. Unfiltered, no-BS, enthusiastic, comedic content for young people excited by the thought of ditching the 9 to 5 — entrepreneurs, content creators, adventurers.

David Powers

Written by

Manufacturing Engineer at ETM Manufacturing, Former Co-Founder and CEO at The Hum, Former Owner at Bleed True LLC, Management Engineering Student at @WPI

The Hum

The Hum

Stories of what it is really like to start your own business, as it happens, without the rose-colored glasses. Unfiltered, no-BS, enthusiastic, comedic content for young people excited by the thought of ditching the 9 to 5 — entrepreneurs, content creators, adventurers.

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